GB1033774A - Preparation of polyols and polyurethane resins - Google Patents
Preparation of polyols and polyurethane resinsInfo
- Publication number
- GB1033774A GB1033774A GB13831/63A GB1383163A GB1033774A GB 1033774 A GB1033774 A GB 1033774A GB 13831/63 A GB13831/63 A GB 13831/63A GB 1383163 A GB1383163 A GB 1383163A GB 1033774 A GB1033774 A GB 1033774A
- Authority
- GB
- United Kingdom
- Prior art keywords
- sucrose
- polyphenol
- alkylene oxide
- alkylene
- mixture
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 229920005862 polyol Polymers 0.000 title abstract 2
- 150000003077 polyols Chemical class 0.000 title abstract 2
- 229920005749 polyurethane resin Polymers 0.000 title 1
- 150000008442 polyphenolic compounds Chemical class 0.000 abstract 11
- 235000013824 polyphenols Nutrition 0.000 abstract 10
- 125000002947 alkylene group Chemical group 0.000 abstract 8
- 239000000203 mixture Substances 0.000 abstract 8
- 150000001875 compounds Chemical class 0.000 abstract 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 5
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 abstract 4
- 229930006000 Sucrose Natural products 0.000 abstract 4
- 239000005720 sucrose Substances 0.000 abstract 4
- 150000001299 aldehydes Chemical class 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 150000003445 sucroses Chemical class 0.000 abstract 3
- 229920001730 Moisture cure polyurethane Polymers 0.000 abstract 2
- 229920005830 Polyurethane Foam Polymers 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 125000005027 hydroxyaryl group Chemical group 0.000 abstract 2
- 229920003986 novolac Polymers 0.000 abstract 2
- 125000005429 oxyalkyl group Chemical group 0.000 abstract 2
- 229920002635 polyurethane Polymers 0.000 abstract 2
- 239000004814 polyurethane Substances 0.000 abstract 2
- 239000011496 polyurethane foam Substances 0.000 abstract 2
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 abstract 1
- 229930185605 Bisphenol Natural products 0.000 abstract 1
- 239000004604 Blowing Agent Substances 0.000 abstract 1
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000003995 emulsifying agent Substances 0.000 abstract 1
- 239000006260 foam Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000003208 petroleum Substances 0.000 abstract 1
- 239000005056 polyisocyanate Substances 0.000 abstract 1
- 229920001228 polyisocyanate Polymers 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 229920005989 resin Polymers 0.000 abstract 1
- 239000011347 resin Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000004094 surface-active agent Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
- C07H15/08—Polyoxyalkylene derivatives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/487—Polyethers containing cyclic groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/54—Polycondensates of aldehydes
- C08G18/546—Oxyalkylated polycondensates of aldehydes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
The invention comprises a mixture of oxyalkylated polyhydroxy compounds, one of said polyhydroxy compounds being a polyphenol containing 2 or more hydroxyaryl groups attached to one or more alkylene radicals and another sucrose, said oxyalkylation being effected with an alkylene oxide of 2-4 carbon atoms until at least one molecule of alkylene oxide per hydroxyl group of sucrose and of the polyphenol has been introduced, and a composition obtained by mixing a partially oxyalkylated sucrose and a polyphenol, as defined above, and oxyalkylating the mixture with an alkylene oxide of 2-4 carbon atoms until the number of oxyalkyl groups introduced exceeds the number of hydroxy groups in the starting polyhydroxy compounds. Suitable polyphenols are those of the formula <FORM:1033774/C2/1> where R is alkylene of M.W. up to 700, R1 is C1- 12 alkyl or halogen, m is 1-3, n is 0-3, x is 1-3 and y is 0-6, one preferred class being the Novolac resins obtained by condensing polyhydroxy phenol and an aldehyde. Many other polyphenols are specified, including bisphenols and the products obtained by condensing a phenol with an unsaturated aldehyde, an hydroxy-aldehyde, a dialdehyde or petroleum resins. The partially oxyalkylated sucrose reactant may have the formula <FORM:1033774/C2/2> where R is hydrogen or C1- 2 alkyl, x is 0-6 and z+y is 3-8. The preferred products are those in which not more than 4 moles alkylene oxide per available hydroxy group are introduced. The novel products are used in the preparation of polyurethane foams (see Division C3). Table I describes a number of products.ALSO:The invention comprises a polyurethane made from a polyisocyanate and a polyol which is (a) a mixture of oxyalkylated polyhydroxy compounds, one of said polyhydroxy compounds being sucrose and the other a polyphenol containing 2 or more hydroxyaryl groups attached to 1 or more alkylene radicals, said oxyalkylation being such that at least one molecule of a C2- 4 alkylene oxide is introduced per hydroxy group of the sucrose and polyphenol, or (b) a composition obtained by oxyalkylating a mixture of a partially oxyalkylated sucrose and a polyphenol, as defined above, using a C2- 4 alkylene oxide until the number of oxyalkyl groups introduced exceeds the number of hydroxy groups in the initial mixture. Suitable polyphenols are those of the formula <FORM:1033774/C3/1> where R is alkylene of M.W. up to 700, R1 is C1- 12 alkyl or halogen, m is 1-3, n is 0-3, x is 1-3 and y is 0-6, one preferred class being the Novolac resins obtained by condensing an aldehyde with a polyphenol. The polyurethanes may be made by the pre-polymer or one-shot technique. A catalyst is used in the final curing, e.g. an amine or an organic salt of tin. Polyurethane foams are made using a blowing agent and a surfactant and/or an emulsifier. Numerous pre-polymer compositions and foams are described in the examples.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US187935A US3265641A (en) | 1962-04-16 | 1962-04-16 | Polyurethanes prepared from a mixture of a sucrose polyether polyol and an oxyalkylated polyphenol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1033774A true GB1033774A (en) | 1966-06-22 |
Family
ID=22691092
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB13831/63A Expired GB1033774A (en) | 1962-04-16 | 1963-04-08 | Preparation of polyols and polyurethane resins |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3265641A (en) |
| AT (1) | AT271908B (en) |
| BE (1) | BE631119A (en) |
| DE (1) | DE1520529A1 (en) |
| FR (1) | FR1360415A (en) |
| GB (1) | GB1033774A (en) |
| NL (1) | NL291318A (en) |
| SE (1) | SE310263B (en) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3433751A (en) * | 1965-02-01 | 1969-03-18 | Takeda Chemical Industries Ltd | Polyether polyol composition and polyurethane foams produced therefrom |
| US3436361A (en) * | 1966-06-09 | 1969-04-01 | Allied Chem | Quick drying urethane coatings |
| US3449318A (en) * | 1966-11-21 | 1969-06-10 | Staley Mfg Co A E | Hydroxyalkylation of (a) polyhydric alcohols using hydrogen fluoride catalyst and (b) dextrose |
| US3516952A (en) * | 1967-04-03 | 1970-06-23 | Cpc International Inc | Curable and cured epoxy-carbohydrate polyether resin compositions |
| US3507817A (en) * | 1967-05-01 | 1970-04-21 | Cpc International Inc | Acrylic-epoxy-carbohydrate polyether coating compositions |
| DE2450540C2 (en) * | 1974-10-24 | 1982-10-14 | Bayer Ag, 5090 Leverkusen | Compositions containing hydroxyl groups and their use for the production of flame-retardant plastics |
| US4239907A (en) * | 1979-01-15 | 1980-12-16 | Bedoit William C Jr | Preparation of low viscosity polyether polyols |
| US4273882A (en) * | 1980-06-02 | 1981-06-16 | Olin Corporation | Preparation of thermally stable rigid polyurethane foam |
| US4309532A (en) * | 1980-09-02 | 1982-01-05 | Texaco Inc. | Modification of amino polyols with epoxy resins |
| JP2613441B2 (en) * | 1988-07-18 | 1997-05-28 | トヨタ自動車株式会社 | Manufacturing method of foamed polyurethane |
| US5474915A (en) * | 1990-05-08 | 1995-12-12 | University Of Iowa Research Foundation | Method of making poly(sugar acrylates) using hydrolytic enzymes |
| US5618933A (en) * | 1990-05-08 | 1997-04-08 | University Of Iowa Research Foundation | Sugar-based polymers |
| US5270421A (en) * | 1990-05-08 | 1993-12-14 | University Of Iowa Research Foundation | Sugar-based polymers |
| WO1992021765A1 (en) * | 1991-05-28 | 1992-12-10 | University Of Iowa Research Foundation | Sugar-based polymers |
| US5690855A (en) * | 1994-01-11 | 1997-11-25 | Sealed Air Corporation | Polyol blend, cellular polyurethane foam product made therefrom, and halogenated hydrocarbon-free process therefor |
| JPH09188736A (en) * | 1996-01-08 | 1997-07-22 | Nippon Paint Co Ltd | Cationic electrodeposition coating excellent in surface smoothness |
| JP3583221B2 (en) * | 1996-02-15 | 2004-11-04 | 三洋化成工業株式会社 | Filling material for cable |
| WO2002026864A1 (en) * | 2000-09-28 | 2002-04-04 | Sanyo Chemical Industries, Ltd. | Polyether, active-hydrogen ingredient, resin-forming composition, and process for producing foam |
| CN102066490B (en) | 2008-06-16 | 2013-09-04 | 三洋化成工业株式会社 | Polymer polyol and method for producing polyurethane |
| WO2010114703A1 (en) * | 2009-04-01 | 2010-10-07 | Dow Global Technologies Inc. | Polyurethane and polyisocyanurate foams having improved curing performance and fire behavior |
| CN102762622A (en) | 2010-02-23 | 2012-10-31 | 三洋化成工业株式会社 | Strength-improving agent for production of polyurethane foam |
| EP2562193B1 (en) | 2010-04-22 | 2018-10-17 | Sanyo Chemical Industries, Ltd. | Polyol for polyurethane preparation and polyurethane preparation method using same |
| EP2671900B1 (en) | 2011-01-31 | 2016-08-10 | Sanyo Chemical Industries, Ltd. | Polyol composition for production of polyurethane resins, and polyurethane resin producing process using same |
| EP2730597B1 (en) | 2011-07-08 | 2018-06-13 | Sanyo Chemical Industries, Ltd. | Polyurethane resin for moisture-permeable water-proof materials, and polyurethane resin composition |
| WO2013018747A1 (en) | 2011-08-02 | 2013-02-07 | 三洋化成工業株式会社 | Powdered polyurethane urea resin composition for slush molding and manufacturing process therefor |
| CN104203999B (en) | 2012-03-29 | 2016-10-12 | 三洋化成工业株式会社 | Vinyl resin and resin combination |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3072582A (en) * | 1955-10-20 | 1963-01-08 | Gen Tire & Rubber Co | Polyether-urethane foams and method of making same |
| US2902478A (en) * | 1957-05-09 | 1959-09-01 | Dow Chemical Co | Oxyalkylation of solid polyols |
| NL254612A (en) * | 1959-08-12 | |||
| US3073788A (en) * | 1959-11-17 | 1963-01-15 | Union Carbide Corp | Polyurethane foams |
| US3164558A (en) * | 1960-03-10 | 1965-01-05 | Dow Chemical Co | Self-extinguishing urethane polymer compositions |
| US3085085A (en) * | 1960-05-03 | 1963-04-09 | Pittsburgh Plate Glass Co | Method of preparing polyethers of mono and disaccharides |
| GB930397A (en) * | 1960-06-09 | 1900-01-01 |
-
0
- BE BE631119D patent/BE631119A/xx unknown
- NL NL291318D patent/NL291318A/xx unknown
-
1962
- 1962-04-16 US US187935A patent/US3265641A/en not_active Expired - Lifetime
-
1963
- 1963-04-08 GB GB13831/63A patent/GB1033774A/en not_active Expired
- 1963-04-11 FR FR931354A patent/FR1360415A/en not_active Expired
- 1963-04-13 DE DE19631520529 patent/DE1520529A1/en active Pending
- 1963-04-16 AT AT308863A patent/AT271908B/en active
- 1963-04-16 SE SE4125/63A patent/SE310263B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE1520529A1 (en) | 1969-11-27 |
| AT271908B (en) | 1969-06-25 |
| FR1360415A (en) | 1964-05-08 |
| NL291318A (en) | |
| US3265641A (en) | 1966-08-09 |
| SE310263B (en) | 1969-04-21 |
| BE631119A (en) |
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